Water → HCID 23144352, compound

HRID 337447Notes

Reaction equation

HRID 337447 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[S:12][C:13]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:14]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[O:9])=[CH:4][N:3]=1.[OH2:29]>N1CCOCC1>[C:21]([C:13]1[S:12][C:11]([NH:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:3]3[CH2:4][CH2:5][O:29][CH2:7][CH2:2]3)=[N:3][CH:4]=2)=[O:9])=[N:15][C:14]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 962WaterHCID 23144525HCID 23144525, compound

Product 1

HCID 23144352HCID 23144352, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

Conditions

Temperature
80 °C

Procedure

Compound 147 (100 mg, 0.244 mmol) was dissolved in morpholine (1 mL), followed by stirring at 80° C. for 1 hour. Water was added to the reaction system, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1) to afford the entitled Compound 148 (81.0 mg, 72%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-37af9b6844254c5bb4561bb6ca698230
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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